You missed the point my friend.
Bob can see the predictions on the screen.
The machine will make it's prediction based on what it has calculated, but Bob can see the result, but the machine already knows that he sees the result, so it includes that into the equasion, but then agian Bob can still see the result...
In other words:
The machine knows that he knows that it knows that he knows that it knows that he knows... Infinitely... Hence infinite regression.
No. The machine calculates Bob's future including him viewing and trying to change the machine's calculations. Then, in trying to change those outcomes, he'll make those outcomes come about anyways. Though this assumes the mind is the whole universe and ignores the external universe. You'd need to run calculations on every bit of matter in the cosmos to predict exactly how Bob's life will go. This machine can simply predict how Bob will act in certain situations perfectly.